How to Stop Saying ‘Someday’ and Plan That Trip With Your Friends!

The year 2024 feels like an absolute whirlwind. Where did the time go?Today’s episode was inspired by one of my podcast producers, Alison, who told me she loves episodes this time of year that take you behind the scenes, which feels good to me; I want to catch you up on what’s been going on.As you may know, I’ve been struggling with health issues this year, so much of what you’ve been listening to was pre-recorded. But finally, in early November, I got diagnosed with a trio of chronic illnesses: Ehlers-Danlos Syndrome, Mast Cell Activation Syndrome, and Dysautonomia.I had hoped to get more done in 2024, but getting closure on some long-standing issues has been a very good thing. And, even though I didn’t have capacity to work on the podcast very much, it has grown, with listeners from 138 countries and almost 4,000 cities. There’s much in store for 2025, but I need your help. Please take my two-minute survey. Do you like solo episodes? Interviews? Grouped topics? Let me know so I can provide the content you crave. I hope the end of your year is filled with ease. See you in 2025.In this episode you’ll hear about:What this last year has looked like: being ill and finally getting diagnoses; moving; wonderful friendship momentsMy goals 2025: health stability, more investment in my community, and more connection to listeners via social media/internetThings to get out into the world in 2025: Freebies! Printed guides! Audio guides! And also, the book I keep talking about!Stats about the podcast (which has grown without any traditional marketing techniques!) and what I’d like to focus on in the coming year Resources & LinksPlease complete my survey so I can provide the kind of content you’re looking for in 2025.Check out YearCompass, which helps you reflect on the past year and set goals for the next. Listen also to Episode 101 and Episode 108.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

I sobbed in the car about the holidays this week – but not for reasons you might think.Here’s what made me emotional: I am so grateful and excited for the ways we are celebrating our holidays this year. It could not be further from the reasons I’ve car sobbed in years past.Some of you are already excited about the holidays, and I love that for you. But that is not everyone’s experience, and for years, it was not mine. There was a period in my 20s when my partner Michael literally called me the Grinch. Holidays are often reserved for families – so where does that leave those of us who don’t have strong familial ties or want something different?This episode is about how to create holiday traditions with your friends that feel GOOD, with practical advice on how  to initiate these conversations and get the ball moving, with the hope that you too will dream up and work toward your own ideal celebrations, too.In this episode you’ll hear about:My personal relationship and evolution with the holiday season, from being the Grinch to crying in the car out of happiness for my holiday plansWhat I was looking for in my holidays, including togetherness, connection, and splitting the burden of the magic makingThe societal normals that often limit holiday options to family gatherings or solitude, and the third option I’m proposing: holidays with friendsInitiating conversations with friends about getting together for the holidays – which often involves a little vulnerability The importance of patience and openness in creating new holiday traditions with friendsResources & LinksLike what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Traditions are incessant. They HAVE to keep happening. That’s what makes them traditions! So how do you create traditions that stick around month after month, year after year? In my opinion, it’s all about sustainability. Traditions have to be something you can maintain on some level as life changes. Otherwise they fizzle out and aren’t traditions anymore.In this episode, I offer tips on how to create traditions that are sustainable for all the people in your life, from your formal communities to your historic and present friends. Traditions matter. They offer safety and security in our relationships by creating consistency and frequency with which we see each other. They don’t need to be elaborate or expensive or energy intensive; they just need to be meaningful and maintainable. So start small. Be consistent. And let things evolve naturally over time.In this episode you’ll hear about:What traditions look like for formal communities, defined/historic/present friends, etc. Different options for touchpoints: in-person gatherings, text threads, virtual chats, neighborhood walks, porch parties, restaurant outings, etc.My own Thursday morning ritual with my business friends that has morphed into a Monday morning paddleboard meet-upQuestions to ask when trying to decide if a tradition is sustainable – plus, let’s change the energy behind being the initiator! Questions to ask if you’re starting new traditions, including: what connections do you want to deepen? What’s already happening naturally that could be more intentional?Resources & LinksListen to Episode 100 about the Wheel of Connection and Episode 52 about pulling off simple neighborhood gatherings.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

If you’ve listened to this podcast before, then you know the concept of the chosen family is very important to me personally.Some people in my chosen family play a variety of roles. Some play just one. Some are back-ups; others are back-ups for my back-ups. Cumulatively, it all adds up: today I feel more supported than I ever have in my life.I’ve talked about chosen families in other episodes – including Episode 16, about my friend Jeff’s, and Episode 19, about my own – but I’ve never done one like today’s, which delves deep into what a chosen family is; why it’s important; and how to build one yourself.Chosen families are the people who catch you when you fall but also help springboard you to the next level. Even if you already have a strong familial support system, this matters: you could still be part of a chosen family for someone else. Whether you’re building a chosen family out of necessity, like I did, or by choice, they matter. They make our lives richer, our support systems stronger, and our worlds a little bit better.In this episode you’ll hear about:What a chosen family is: people who choose you through their words, intentions, and actions (with you choosing them back)The fallacy of the “all-or-nothing” mindset of the chosen family and the different roles chosen family members can play: big, small, medical, etc.My breast-cancer scare and how I leaned on my chosen family while I had to wait for the mammogram and ultrasoundCelebrating holidays, birthdays, vacations, and milestones with chosen family members and how to create traditions with themWays we can support our chosen families – plus, the power of specific support offers (helping with a new baby; driving someone to doctor appointments, etc.)Resources & LinksListen to other episodes about chosen families, including Episode 19, “The One for Little Alex,” and Episode 16. Also be sure to listen to Episode 12, about my Roots of Connection framework.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

A few years ago, Debra Driscoll was living in Brooklyn, navigating a long-distance relationship and a life split between the city and the sea. Then, in 2020, her world was turned upside down.Instead of seeing this as a setback, Debra took it as an opportunity to fast-forward her dreams and create something beautiful. Now Debra is a spiritual teacher and energy guide who, from her home in Tobago, runs a thriving community, Big Life Magic, which is made up of people who are looking for a space to grow and transform, and for others to witness and celebrate their transformation. Today’s episode is all about finding those spaces where we can truly show up as ourselves – not just who we are now, but who we dream of becoming, filled with people who believe that anything is possible for us.In this episode you’ll hear about:Debra’s split life in New York City until 2020 – followed by her move to Tobago, where she started Big Life Magic, which focuses on spiritual guidance and energy workThe concept of "believing mirrors,” where friends reflect and affirm each other's potential and dreamsNot asking people about past or current selves, but instead: what do you want? Who do you hope to become? And how can I support you to get there?The power of getting out of your bubble and seeing other places, other people, and other ways to be in the worldAdvice for people looking to find similar transformational spaces for themselves and questions to ask themselves, like: what do I want in my life now? What do I need?Resources & LinksLearn about Debra’s company, Big Life Magic, and her book, A Series of Surrendor: a Memoir of Grief.See Friendship IRL Episode 91, “How to Stop Dreading Parties and Take Charge of Your Guest Experience.”Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

Many times on this podcast, I’ve talked about how powerful virtual connection can be, with the caveat: are you ACTUALLY engaging, or are you just lurking? Today we dive into connection through podcasts and social media, emphasizing active over passive consumption. Our guest is Sharon Walters, a coach and author who has made it her mission to transform gratitude from a reaction to an action.In this episode, Sharon highlights the impact of positive feedback and genuine interactions. She uses social media to build meaningful relationships and supports content creators by sharing their work and closing the loop. It’s easy to turn social media and podcasts into passive connections, but actually, they are brimming with opportunities for authentic relationships. There are real people behind the microphones and cameras, and it only helps to show them some love. So give them a like. Send them a message. You might even make a new friend.In this episode you’ll hear about:What it means to close the loop in virtual connections so that you’re actively participating instead of just lurkingThe possibility of virtual connection: Sharon’s friendships she’s made through social media or podcasts, and my ownMy challenge to you: if you’re listening to a podcast, and it’s not one of the chart-toppers, connect with them: send them a message, give them a likeThe importance of being genuine and authentic in online interactions (and also, the value of positive feedback for content creators)Resources & LinksSharon is a business owner, gratitude coach, fitness trainer, and author. Visit her website and follow her on Facebook and Instagram.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

I just got back from this wild, adventurous, 11-day road trip with my friend to see two Taylor Swift concerts on opposite sides of the country. How did we make it happen? Partly, the stars aligned; partly, we’re privileged in that we’re self-employed, childless, and could afford it; but also, we just went for it. It was so fun and actually inspired a new goal: I want to go on a one-week girls trip sometime this decade.By this point in my life, I’ve traveled a lot. I’ve had so many fun experiences with friends. I was able to do it because I stopped waiting for the stars to align, for that perfect thing to happen. In this episode, I present a special call to stop saying the word someday. Someday I’ll go on that girls trip. Someday I will make it out to visit that friend. Someday we’ll take that vacation. Here, I offer four tips to help you just get that friend trip on the calendar.In this episode you’ll hear about:My trip with my friend: what we did, where we stayed, what the logistics looked like, and why it was so fun (but also, not the norm for friend trips)Starting with small gatherings – Slumber party! Staycation! Weekend away! Board game night! – which can help build momentum for larger tripsInvolving everyone in the process and giving plenty of time to plan for care and work arrangements (and how this can be part of the bonding experience with friends)Making the trip attainable and enjoyable for everyone involved, with focus on connection and relaxation, as opposed to creating the “ideal” vacationResources & LinksInterested in trying a slumber party with your friends? Listen to Episode 28. Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

In this episode, I pull back the curtain on one of my own formal communities: the Toastmasters.Today’s guest is Brendan Smith, a member of the Toastmasters chapter I was part of. Toastmasters is an international speaking club and educational organization, and for four years, Brendan and I met with the group every Thursday: sometimes online, sometimes in person; sometimes as presenters, sometimes as listeners. We all shared a common goal – to become better communicators and speakers – but there was an underlying benefit, too. You get to know people in a formal community. Over time, you develop a feeling of belonging to it.Since talking with Brendan, I have to admit, I did not renew my Toastmasters membership. I was not able to invest in it the way I felt I should have due to work and health stuff I’ve been going through. And though it’s not a part of my weekly schedule anymore, I have such fond memories of the Toastmasters. It will always be a valuable part of my story and community.In this episode you’ll hear about:What a formal community is and the importance of its regularity, from its structure to its shared goalsWhat it was like joining Toastmasters with Brendan early COVID and what our club looked like: the variety of members of different ages, careers, and backgroundsThe importance of discomfort, shared experiences, and informal interactions in building a strong formal communityWhat we learn when we’re experiencing things with people – or talking with them “side-by-side” instead of face-to-faceResources & LinksLike what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

This episode, about navigating friendship through chronic illness, is deeply personal to me.In last week’s episode, I shared about my own recent health issues, but I think this information is good to have no matter your situation. Chances are, chronic illness will impact somebody in your life in your lifetime.Today’s guest is Catherine, a business coach, founder of Catherine LifeDesign, and a survivor of chronic illness. Here, Catherine shares about her “perfect storm” of life events – including a miscarriage and Hashimoto’s disease diagnosis – that resulted in a severe health crash.Chronic illness is hard. There is no exact solution on how to navigate friendships around this; it’s so personal and so nuanced. But my hope is that this one more story out there offers ideas on how to deal with this if it’s impacting your own life.In this episode you’ll hear about:Catherine’s dream life: a successful business, a tropical Mediterranean home – and how it all fell apart with her three-year illness that stumped so many doctorsThe power of the friends who kept calling and asking how she was – a simple thing that offered comfort and support thousands of miles awayThe skill of managing your own emotional state and seeking the right support when you need it (and the importance of supplementing with professional support)The skill of rebuilding relationships, which Catherine learned on her healing journey, and how she views and interacts with friends nowHow friendship roots change when somebody goes through a major life change or illness (and how that impacts the work required to maintain the friendship)Resources & Links:Follow Catherine on Instagram and on her website.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!

This whole podcast was only a dream a couple years ago, and here we are now with 100 episodes. Thank you for being here, for listening, and for sharing these conversations with your friends.In this episode, I share some life updates and talk intensely about the Wheel of Connection (view this visual diagram!), which is a foundational concept to my work. I give an overview about each of the categories, and at the end of the episode, I talk about how to do a basic Wheel of Connection audit. You deserve Level 10 support, and hopefully this helps you to take more intentional action to develop the connections you need for this season of life. Want to go even deeper? Sign up for my newsletter to receive more information, including announcements about my forthcoming book and the Wheel of Connection audio guide.In this episode you’ll hear about:Life updates regarding my health, two Taylor Swift concerts, and the major milestone of this episodeThe Wheel of Connection: why I made it, why it’s round, why it looks different for everyoneHow your own Wheel of Connection is constantly changing: people move between categories, and different categories grow and shrink depending on your needsWheel of Connection components: family of origin; family of choice; formal community; acquaintance; and familiar/defined/present/historic friendHow the Wheel of Connection and Roots Framework work together, and how to conduct a Wheel of Connection auditResources & Links:Here are some visuals of the Wheel of Connection and my Roots framework. Want more? Sign up for my newsletter to receive more information, including announcements about my forthcoming book and the Wheel of Connection audio guide.Like what you hear? Visit my website, leave me a voicemail, and follow me on Instagram and TikTok!Want to take this conversation a step further? Send this episode to a friend. Tell them you found it interesting and use what we just talked about as a conversation starter the next time you and your friend hang out!